HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$118+ Cheap flights from Madison (MSN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Madison to Caribbean Islands

Cheapest flights from Madison to Caribbean Islands
Explore the most affordable flight options available from Madison to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:55 pmMSN - SJU
1 stop15h 44mAmerican Airlines
Fri 1/96:30 amSJU - MSN
1 stop11h 50mAmerican Airlines
Deal found 12/18$380
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:58 amMSN - SJU
2 stops9h 13mAmerican Airlines
Mon 12/228:25 amSJU - MSN
2 stops11h 16mAmerican Airlines
Deal found 12/16$480
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:58 amMSN - SJU
2 stops9h 13mAmerican Airlines
Thu 1/86:00 amSJU - MSN
2 stops11h 27mAmerican Airlines
Deal found 12/16$505
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:23 pmMSN - SJU
2 stops15h 48mUnited Airlines
Fri 1/92:05 amSJU - MSN
2 stops11h 46mUnited Airlines
Deal found 12/17$514
This American Airlines deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/188:00 pmMSN - SJU
1 stop17h 08mAmerican Airlines
Thu 12/256:00 amSJU - MSN
1 stop13h 42mAmerican Airlines
Deal found 12/18$574
This United Airlines deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1812:23 pmMSN - SJU
2 stops10h 13mUnited Airlines
Thu 12/2510:15 amSJU - MSN
2 stops14h 15mUnited Airlines
Deal found 12/18$604
This American Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:00 amMSN - SJU
1 stop13h 05mAmerican Airlines
Thu 12/257:00 amSJU - MSN
1 stop17h 24mAmerican Airlines
Deal found 12/17$632
This United Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:30 amMSN - SJU
2 stops12h 56mUnited Airlines
Fri 12/262:05 amSJU - MSN
2 stops19h 00mUnited Airlines
Deal found 12/16$639
This American Airlines deal was found by Cheapflights users on 12/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amMSN - STT
2 stops9h 39mAmerican Airlines
Sat 1/104:47 pmSTT - MSN
2 stops19h 56mAmerican Airlines
Deal found 12/16$641
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:26 pmMSN - PUJ
2 stops17h 33mUnited Airlines
Fri 12/264:25 pmPUJ - MSN
1 stop8h 05mUnited Airlines
Deal found 12/17$661
This United Airlines deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:00 amMSN - STT
1 stop9h 18mUnited Airlines
Sat 1/103:05 pmSTT - MSN
1 stop8h 00mUnited Airlines
Deal found 12/17$751
This Delta deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:31 amMSN - MBJ
1 stop7h 19mDelta
Thu 1/12:55 pmMBJ - MSN
1 stop8h 14mDelta
Deal found 12/17$775

Find flight deals from Madison to Caribbean Islands

Keep the following information in mind while searching for Madison to Caribbean Islands flight deals. Data was last updated December 18, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$118
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$619
From Madison Truax Field to Caribbean Islands
Search Deals
One-way flight from Madison Truax Field to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
Use the filters below to find and compare flights from Madison to Caribbean Islands that are best for you.

Fly from

Madison

Fly to

Caribbean Islands

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/24

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Tue 3/3

8:35 am-2:07 pm

1 stop7h 32m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/24

8:09 am-8:36 pm

2 stops10h 27m

San Juan Luis Munoz Marin Intl

Wed 3/4

7:00 am-4:51 pm

2 stops11h 51m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 3/3

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Tue 3/10

1:05 am-2:02 pm

2 stops13h 57m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 2/23

6:30 am-10:22 pm

2 stops13h 52m

San Juan Luis Munoz Marin Intl

Mon 3/2

2:05 am-11:53 am

2 stops11h 48m

$272

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Thu 1/22

9:50 am-11:45 pm

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Tue 1/27

4:30 pm-10:50 pm

1 stop8h 20m

$278

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Fri 1/2

8:10 pm-3:08 pm

1 stop16h 58m

San Juan Luis Munoz Marin Intl

Wed 1/21

6:30 am-4:20 pm

1 stop11h 50m

$317

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 3/23

10:49 am-9:22 pm

2 stops9h 33m

San Juan Luis Munoz Marin Intl

Sun 3/29

7:40 am-3:05 pm

1 stop8h 25m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 5/2

6:30 am-8:38 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

Tue 5/5

1:00 am-10:11 am

2 stops10h 11m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/27

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:10 am-7:07 pm

2 stops12h 57m

$325

MadisonPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 3/3

5:38 am-3:30 pm

1 stop7h 52m

Punta Cana

Tue 3/10

1:45 pm-10:58 pm

1 stop10h 13m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Madison to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Caribbean Islands

What is the cheapest month to book a flight from Madison to Caribbean Islands?

Currently, November is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $113). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $379). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MSN to EPX?

Find hourly flight availability from Madison to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Madison to Caribbean Islands at noon. If you’re flexible enough to do this you can expect to save up to 25% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated December 18, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Madison to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,005 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,091 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,005 reviews

Overall

7.9

Boarding

8.1

Crew

8.5

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Caribbean Islands?

    Madison Truax Field (MSN) is the airport you will fly out of if you book a flight from Madison to Caribbean Islands. It is only a 5.4 mi journey to Truax Field (MSN) from Madison’s city center.

  • How long is the flight from Madison to Caribbean Islands?

    A quick flight from Madison to Caribbean Islands can take about 7h 10m. United Airlines provides one of the quickest options available for as low as $235. There are 2180 mi between Madison and Caribbean Islands. This flight may include one or multiple stops.

  • What are the most popular routes from Madison to Caribbean Islands?

    While some choose either Madison Truax Field - Punta Cana or Madison Truax Field - Saint Thomas Island Cyril E King, Madison Truax Field - San Juan Luis Munoz Marin Intl is the most popular route from Madison to Caribbean Islands.

  • Can I find deals for flights from Madison to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Madison to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Caribbean Islands.

  • Can I find deals for business class flights from Madison to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Madison to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Caribbean Islands?

    Currently, November is the cheapest month in which you can book a flight from Madison to Caribbean Islands (average of $113). Flying from Madison to Caribbean Islands in June is currently the most expensive (average of $379). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
Minneapolis to Sky Harbor Intl flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Orlando flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Miami flights
Minneapolis to Orlando flights
Minneapolis to Cancún flights
O'Hare Intl to Tampa flights
Minneapolis to Las Vegas flights
Minneapolis to Miami flights
O'Hare Intl to Denver flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Minneapolis to Fort Myers flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Atlanta flights
Minneapolis to Dallas/Fort Worth flights
Minneapolis to Tampa flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to Ontario flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Seattle flights
Minneapolis to Los Angeles flights
O'Hare Intl to San Diego flights
Minneapolis to San Diego flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to Honolulu flights
Minneapolis to LaGuardia flights
Milwaukee to Orlando flights
O'Hare Intl to Love Field flights
O'Hare Intl to Cozumel flights
O'Hare Intl to West Palm Beach flights
Minneapolis to Denver flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Hobby flights
Minneapolis to Newark flights
Minneapolis to Honolulu flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to New Orleans flights
Milwaukee to Las Vegas flights
Minneapolis to Seattle flights

Top 3 airlines flying from Madison to Caribbean Islands

Discover the top 3 airlines that operate flights from Madison to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$752FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$654FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$652FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.